Fungicidal n-(2-pyridylpropyl) carboxamide derivatives and their oxa, aza and thia analogues

ABSTRACT

The present invention relates to fungicide N-(2-pyridylpropyl)carboxamide derivative and its oxa, aza and thia analogues of formula (I), their process of preparation and intermediate compound for their preparation, their use as fungicides, particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions. 
     
       
         
         
             
             
         
       
     
     wherein A, T, W, X, n and Z 3  to Z 7  represent various substituents.

The present invention relates to fungicideN-(2-pyridylpropyl)carboxamide derivatives, their oxa, aza and thiaanalogues, their process of preparation and intermediate compounds fortheir preparation, their use as fungicides, particularly in the form offungicidal compositions and methods for the control of phytopathogenicfungi of plants using these compounds or to their compositions.

In Japanese patent application JP-2001/348378 certain fungicidalN-hetarylalkylcarboxamide derivatives are generically embraced in abroad disclosure of numerous compounds of the following formula:

wherein X can represent the group NH, A can represent a C₁-C₁₂-alkylenechain and R can represent an (un)substituted pyridyl group. However,this document does not disclose compounds wherein the nitrogen atom ofthe carboxamide residue can be substituted by a cycloalkyl group.

In Japanese patent application JP-2001/342180 certain fungicidalN-hetarylalkylcarboxamide derivatives are generically embraced in abroad disclosure of numerous compounds of the following formula:

wherein A can represent a C₁-C₁₂-alkylene chain and R can represent an(un)substituted pyridyl group. However, this document does not disclosecompounds wherein the nitrogen atom of the carboxamide residue can besubstituted by a cycloalkyl group.

In international patent application WO-2006/098128 certain fungicidalN-hetarylalkylcarboxamide and thiocarboxamide derivatives aregenerically embraced in a broad disclosure of numerous compounds of thefollowing formula:

wherein W₁ can represent an oxygen or a sulfur atom, Y can represent thegroup NR¹¹ where R¹¹ can represent hydrogen, alkyl, cycloalkyl or thelike, and R⁷ can represent an (un)substituted heterocyclyl C₁-C₆-alkylgroup. However, this document does not specifically disclose nor suggestto select such compounds wherein R¹¹ can be a cycloalkyl group.

In international patent application WO-1997/08147 certain fungicidalN-(2-pyridylthio)alkylcarboxamide derivatives are generically embracedin a broad disclosure of numerous compounds of the following formula:

wherein m can take a value of 0, 1 or 2, ALK can represent a C₂-C₃-alkylgroup, X can represent the group NR⁵ where R⁵ can represent hydrogen,alkyl or cycloalkyl, and Q can represent an aryl or a heteroaryl group.However, this document does not specifically disclose nor suggest toselect such compounds wherein R⁵ can be a cycloalkyl group, nor doesthis document specifically disclose or suggest to select such compoundswherein Q can be a heteroaryl group.

In international patent application WO-2009/012998 certain fungicidalN-([het]aryloxy)alkylcarboxamide derivatives are generically embraced ina broad disclosure of numerous compounds of the following formula:

wherein A is a 5-membered heterocyclic ring, R₁₅ can represent hydrogenor cycloalkyl, R₁, R₂, R₃ and R₄ can represent hydrogen, alkyl, halogenand the like, and B can represent an aryl or a heteroaryl group.However, this document does not specifically described any physical orbiological properties of compounds wherein R₁₅ is a cycloalkyl group.

It is always of high-interest in the field of agrochemicals to usepesticidal compounds more active than the compounds already known by theman ordinary skilled in the art whereby reduced amounts of compound canbe used whilst retaining equivalent efficacy.

Furthermore, the provision of new pesticidal compounds with a higherefficacy strongly reduces the risk of appearance of resistant strains inthe fungi to be treated. We have now found a new family of compoundswhich show enhanced fungicidal activity over the general known family ofsuch compounds.

Accordingly, the present invention provides aN-(2-pyridylpropyl)carboxamide derivative and its oxa, aza and thiaanalogues of formula (I)

wherein

-   -   A represents a carbo-linked, unsaturated or partially saturated,        5-membered heterocyclyl group that can be substituted by up to        four groups R;    -   T represents O or S;    -   W represents CZ¹Z², O, S, SO, SO₂ or N—R^(a);    -   n represents 0, 1, 2, 3 or 4;    -   X represents a halogen atom, a nitro, a cyano, an isonitrile, a        hydroxy, an amino, a sulfanyl, a pentafluoro-λ⁶-sulfanyl, a        formyl, a formyloxy, a formylamino, a carboxy, a carbamoyl, a        N-hydroxycarbamoyl, a carbamate, a (hydroxyimino)-C₁-C₆-alkyl, a        C₁-C₈-halogenoalkyl having 1 to 9 halogen atoms, a C₁-C₈-alkyl,        a C₂-C₈-alkenyl, a C₂-C₈-halogenoalkenyl comprising up to 9        halogen atoms that can be the same or different, a        C₂-C₈-alkynyl, a C₂-C₈-halogenoalkynyl comprising up to 9        halogen atoms that can be the same or different, a        C₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, a        C₁-C₈-halogenoalkoxy having 1 to 9 halogen atoms, a        C₁-C₈-alkoxy-C₁-C₈-alkyl, a C₁-C₈-alkoxy-C₁-C₈-alkoxy, a        C₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanyl having 1 to 9        halogen atoms, a C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy        having 1 to 9 halogen atoms, a C₂-C₈-alkynyloxy, a        C₂-C₈-halogenoalkynyloxy having 1 to 9 halogen atoms, a        C₃-C₈-cycloalkyl, a C₃-C₇-cycloalkyl-C₂-C₈-alkenyl, a        C₃-C₇-cycloalkyl-C₂-C₈-alkynyl, a C₃-C₈-halogenocycloalkyl        having 1 to 9 halogen atoms, a        C₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl, a        C₁-C₈-alkyl-C₃-C₇-cycloalkyl, a C₆-C₁₄-bicycloalkyl, a        C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to 9        halogen atoms, a C₁-C₈-alkylcarbamoyl, a        di-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, a        C₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a        C₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxy carbonyl having 1        to 9 halogen atoms, a C₁-C₈-alkylcarbonyloxy, a        C₁-C₈-halogenoalkylcarbonyloxy having 1 to 9 halogen atoms, a        C₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino        having 1 to 9 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, a        di-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, a        C₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to        9 halogen atoms, a C₁-C₈-alkylsulphinyl, a        C₁-C₈-halogenoalkylsulphinyl having 1 to 9 halogen atoms, a        C₁-C₈-alkylsulphonyl, a C₁-C₈-halogenoalkylsulphonyl having 1 to        9 halogen atoms, a C₁-C₈-alkoxyimino, a        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, a        (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl, a        (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a        (benzyloxyimino)-C₁-C₈-alkyl, a tri(C₁-C₈-alkyl)silyl, a        tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, a benzyloxy that can be        substituted by up to 5 groups Q, a benzylsulfanyl that can be        substituted by up to 5 groups Q, a benzylamino that can be        substituted by up to 5 groups Q, an aryl that can be substituted        by up to 5 groups Q, an aryloxy that can be substituted by up to        5 groups Q, an arylamino that can be substituted by up to 5        groups Q, an arylsulfanyl that can be substituted by up to 5        groups Q, an aryl-C₁-C₈-alkyl that can be substituted by up to 5        groups Q, an aryl-C₂-C₈-alkenyl that can be substituted by up to        5 groups Q, an aryl-C₂-C₈-alkynyl that can be substituted by up        to 5 groups Q, an aryl-C₃-C₇-cycloalkyl that can be substituted        by up to 5 groups Q, a pyridinyl that can be substituted by up        to 4 groups Q or a pyridinyloxy that can be substituted by up to        4 groups Q;    -   Z¹ and Z² independently represent a hydrogen atom, a halogen        atom, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a        C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a        C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5        halogen atoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen        atoms or a C₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms;    -   Z³ and Z⁴ are chosen independently of each other as being a        hydrogen atom, a halogen atom, a C₁-C₈-halogenoalkyl having 1 to        5 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a        C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl        having 1 to 5 halogen atoms, a C₁-C₈-halogenoalkenyl having 1 to        5 halogen atoms or a C₁-C₈-halogenoalkynyl having 1 to 5 halogen        atoms;    -   Z⁵ and Z⁶ independently represent a hydrogen atom, a        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl,        a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a        C₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a        C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or a        C₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms;    -   Z⁷ represents a non-substituted C₃-C₇-cycloalkyl or a        C₃-C₇-cycloalkyl substituted by up to 10 atoms or groups that        can be the same or different and that can be selected in the        list consisting of halogen atoms; cyano; C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be        the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkylaminocarbonyl; or        di-C₁-C₈-alkylaminocarbonyl;    -   R^(a) represents a hydrogen atom; C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be        the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl        comprising up to 9 halogen atoms that can be the same or        different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl;        C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that        can be the same or different; formyl; C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylsulphonyl;        C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms        that can be the same or different; aryl that can be substituted        by up to 5 groups Q; phenylmethylene that can be substituted by        up to 7 groups Q; or phenylsulphonyl that can be substituted by        up to 5 groups Q;    -   Q independently represents a halogen atom; cyano; isonitrile;        nitro; C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-alkynyl; C₁-C₈-alkoxy;        C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkoxy-C₁-C₈-alkoxy;        C₁-C₈-alkylsulfanyl C₁-C₈-halogenoalkyl comprising up to 9        halogen atoms that can be the same or different;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-halogenoalkynyl comprising up to        9 halogen atoms that can be the same or different;        C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can        be the same or different; C₁-C₈-halogenoalkylsulfanyl comprising        up to 9 halogen atoms that can be the same or different;        C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen        atoms that can be the same or different; tri(C₁-C₈)alkylsilyl        and tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; C₁-C₈-alkoxyimino; or        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;    -   R independently represents a hydrogen atom; halogen atom; cyano;        isonitrile; nitro; amino; sulfanyl pentafluoro-λ⁶-sulfanyl        C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; tri(C₁-C₈-alkyl)silyl;        C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl comprising up        to 9 halogen atoms that can be the same or different;        C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen        atoms that can be the same or different; C₂-C₈-alkenyl;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9        halogen atoms that can be the same or different;        C₂-C₈-alkenyloxy; C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl;        C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₁-C₈-alkylsulphinyl;        C₁-C₈-alkylsulphonyl; C₁-C₈alkoxyimino;        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; (benzyloxyimino)-C₁-C₈-alkyl;        aryloxy; benzyloxy; benzylsulfanyl; benzylamino; aryl;        halogenoaryloxy comprising up to 9 halogen atoms that can be the        same or different; C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkoxycarbonyl;        C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylaminocarbonyl; or        di-C₁-C₈-alkylaminocarbonyl;    -   with the provisio that when W is oxygen, T is oxygen and n is        greater or equal to 1, then X is not a halogen atom, a nitro, a        cyano, an amino, a formyl, a (hydroxyimino)-C₁-C₆-alkyl, a        C₁-C₆-alkyl, a C₁-C₆-halogenoalkyl, a C₂-C₆-alkenyl, a        C₂-C₆-halogenoalkenyl, a C₂-C₆-alkynyl, a C₂-C₆-halogenoalkynyl,        a C₁-C₆-alkylamino, a di-C₁-C₆-alkylamino, a C₁-C₆-alkoxy, a        C₁-C₆-halogenoalkoxy, a C₁-C₆-alkoxy-C₁-C₆-alkyl, a        C₁-C₆-alkylsulfanyl, a C₂-C₆-alkenyloxy, a        C₂-C₆-halogenoalkenyloxy, a C₃-C₆-cycloalkyl, a        C₃-C₆-cycloalkyl-C₂-C₆-alkenyl, a        C₃-C₆-cycloalkyl-C₂-C₆-alkynyl, a C₃-C₆-halogenocycloalkyl, a        C₃-C₆-cycloalkyl-C₃-C₆-cycloalkyl, a        C₁-C₆-alkyl-C₃-C₆-cycloalkyl, a C₆-C₁₄-bicycloalkyl, a        C₁-C₆-alkylcarbonyl, a C₁-C₆-alkylcarbonylamino, a        (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a        tri(C₁-C₆-alkyl)silyl-C₁-C₆-alkyl, a phenyl that can be        substituted by one or more groups G, a phenoxy that can be        substituted by up one or more groups G, a phenyl-C₁-C₆-alkyl        that can be substituted by one or more halogens, a        phenyl-C₂-C₆-alkenyl that can be substituted by one or more        halogens, a phenyl-C₂-C₆-alkynyl that can be substituted by one        or more halogens, a phenyl-C₃-C₆-cycloalkyl that can be        substituted by one or more halogens; each G independently        represents a halogen, nitro, C₁-C₆-alkoxy, C₁-C₆-alkylsulfanyl,        C₁-C₆-halogenoalkoxy, C₁-C₆-halogenoalkyl sulfanyl,        tri(C₁-C₆₋alkyl)silyl, (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl;

as well as its salts, N-oxydes, metallic complexes, metalloidiccomplexes and optically active isomers.

For the compounds according to the invention, the following genericterms are generally used with the following meanings:

-   -   halogen means fluorine, bromine, chlorine or iodine.    -   carboxy means —C(═O)OH;    -   carbonyl means —C(═O)—;    -   carbamoyl means —C(═O)NH₂;    -   N-hydroxycarbamoyl means —C(═O)NHOH;    -   SO₂ represents a sulfoxyde group;    -   SO₂ represents a sulfone group;    -   an alkyl group, an alkenyl group and an alkynyl group as well as        moieties containing these terms, can be linear or branched;    -   the term aryl means phenyl or naphthyl;    -   heteroatom means sulphur, nitrogen or oxygen.    -   in the case of an amino group or the amino moiety of any other        amino-comprising group, substituted by two substituents that can        be the same or different, the two substituents together with the        nitrogen atom to which they are linked can form a heterocyclyl        group, preferably a 5- to 7-membered heterocyclyl group, that        can be substituted or that can include other hetero atoms, for        example a morpholino group or piperidinyl group.

Any of the compounds of the present invention can exist in one or moreoptical or chiral isomer forms depending on the number of asymmetriccentres in the compound. The invention thus relates equally to all theoptical isomers and to their racemic or scalemic mixtures (the term“scalemic” denotes a mixture of enantiomers in different proportions)and to the mixtures of all the possible stereoisomers, in allproportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods which are known per se by the manordinary skilled in the art.

Any of the compounds of the present invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

Any of the compounds of formula (I) wherein X represents a hydroxygroup, a sulfanyl group or an amino group may be found in its tautomericform resulting from the shift of the proton of said hydroxy, sulfanyl oramino group. Such tautomeric forms of such compounds are also part ofthe present invention. More generally speaking, all tautomeric forms ofcompounds of formula (I) wherein X represents a hydroxy group, asulfanyl group or an amino group, as well as the tautomeric forms of thecompounds which can optionally be used as intermediates in thepreparation processes and which will be defined in the description ofthese processes, are also part of the present invention.

Preferred compounds according to the invention are compounds of formula(I) wherein A is selected in the list consisting of:

a heterocycle of formula (A¹)

wherein:

R¹ to R³ that can be the same or different represent a hydrogen atom; ahalogen atom; C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

a heterocycle of formula (A²)

wherein:

R⁴ to R⁶ that can be the same or different represent a hydrogen atom; ahalogen atom; C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

a heterocycle of formula (A³)

wherein:

R⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to9 halogen atoms that can be the same or different; R⁹ represents ahydrogen atom or a C₁-C₅-alkyl;

a heterocycle of formula (A⁴)

wherein:

R⁹ to R¹¹ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C₅-alkyl; amino; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogenatoms that can be the same or different;

a heterocycle of formula (A⁵)

wherein:

R¹² and R¹³ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

R¹⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different or C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;

a heterocycle of formula (A⁶)

wherein:

R¹⁵ represents a hydrogen atom; a halogen atom; a cyano; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; R¹⁶ and R¹⁸ that can bethe same or different represent a hydrogen atom; a halogen atom;C₁-C₅-alkoxycarbonyl; C₁-C₅-halogenoalkoxy comprising up to 9 halogenatoms that can be the same or different or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

R¹⁷ represent a hydrogen atom or C₁-C₅-alkyl;

a heterocycle of formula (A⁷)

wherein:

R¹⁹ represents a hydrogen atom or a C₁-C₅-alkyl

R²⁹ to R²² that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

a heterocycle of formula (A⁸)

wherein:

R²³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

R²⁴ represents a hydrogen atom or C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

a heterocycle of formula (A⁹)

wherein:

R²⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

R²⁶ represents a hydrogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

a heterocycle of formula (A¹⁰)

wherein:

R²⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

R²⁸ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; C₁-C₅-alkylamino ordi(C₁-C₅-alkyl)amino;

a heterocycle of formula (A¹¹)

wherein:

R²⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

R³⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; C₁-C₅-alkylamino ordi(C₁-C₅-alkyl)amino;

a heterocycle of formula (A^(l2))

wherein:

R³¹ represents a hydrogen atom or a C₁-C₅-alkyl

R³² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

R³³ represents a hydrogen atom; a halogen atom; a nitro; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

a heterocycle of formula (A¹³)

wherein:

R³⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C3-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

R³⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano;C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;

R³⁶ represents a hydrogen atom or C₁-C₅-alkyl;

a heterocycle of formula (A¹⁴)

wherein:

R³⁷ and R³⁸ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy or aC₁-C₅-alkylsulphanyl;

R³⁹ represents a hydrogen atom or C₁-C₅-alkyl;

a heterocycle of formula (A¹⁵)

wherein:

R⁴⁰ and R⁴¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

a heterocycle of formula (A¹⁶)

wherein:

R⁴² and R⁴³ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different or amino;

a heterocycle of formula (A¹⁷)

wherein:

R⁴⁴ and R⁴⁵ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

a heterocycle of formula (A¹⁸)

wherein:

R⁴⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

R⁴⁶ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-alkylsulfanyl

a heterocycle of formula (A¹⁹)

wherein:

R⁴⁹ and R⁴⁸ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

a heterocycle of formula (A²⁰)

wherein:

R⁵⁰ and R⁵¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

heterocycle of formula (A²¹)

wherein:

R⁵² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different.

a heterocycle of formula (A²²)

wherein:

R⁵³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different.

a heterocycle of formula (A²³)

wherein:

R⁵⁴ and R⁵⁶ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

R⁵⁵ represents a hydrogen atom or C₁-C₅-alkyl;

a heterocycle of formula (A²⁴)

wherein:

R⁵⁷ and R⁵⁹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

R⁵⁸ represents a hydrogen atom or C₁-C₅-alkyl;

a heterocycle of formula (A²⁵)

wherein:

R⁶⁰ and R⁶¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

R⁶² represents a hydrogen atom or C₁-C₅-alkyl;

a heterocycle of formula (A²⁶)

wherein:

R⁶⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

R⁶³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano;C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;

R⁶⁴ represents a hydrogen atom or C₁-C₅-alkyl.

More preferred compounds according to the invention are compounds offormula (I) wherein A is selected in the list consisting of A²; A⁶; A¹⁰and A¹³ as herein-defined.

Even more preferred compounds according to the invention are compoundsof formula (I) wherein A represents A¹³ wherein R³⁴ represents aC₁-C₅-alkyl, C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; C₁-C₅-alkoxy; R³⁵ represents a hydrogenatom or a halogen atom and R³⁶ represents a C₁-C₅-alkyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein W represents O or S.

Other preferred compounds according to the invention are compounds offormula (I) wherein W represents CZ¹Z² wherein Z¹ and Z² are asherein-defined.

Other preferred compounds according to the invention are compounds offormula (I) wherein n represents 0, 1 or 2.

Other preferred compounds according to the invention are compounds offormula (I) wherein X independently represents a halogen atom;C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkoxy orC₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different.

Other more preferred compounds according to the invention are compoundsof formula (I) wherein two consecutive substituents X together with thephenyl ring form a substituted or non substituted 1,3-benzodioxolyl;1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl;1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; or indolinyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z¹ and Z² independently represent a hydrogen atom ora C₁-C₈-alkyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z³ and Z⁴ independently represent a hydrogen atom ora C₁-C₈-alkyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z⁵ and Z⁶ independently represent a hydrogen atom ora C₁-C₈-alkyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z⁷ represents a non-substituted C₃-C₇ cycloalkyl; aC₃-C₇ cycloalkyl substituted by up to 10 groups or atoms that can be thesame or different and that can be selected in the list consisting ofhalogen atoms; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₈-alkoxy orC₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; more preferably Z⁷ represents a non-substitutedC₃-C₇-cycloalkyl; even more preferably Z⁷ represents cyclopropyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein R independently represents a hydrogen atom; halogenatom; cyano; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino;tri(C₁-C₈-alkyl)silyl; C₁-C₈-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-alkylsulfanyl; amino, hydroxyl; nitro;C₁-C₈-alkoxycarbonyl; C₂-C₈-alkynyloxy.

The above mentioned preferences with regard to the substituents of thecompounds according to the invention can be combined in various manners.These combinations of preferred features thus provide sub-classes ofcompounds according to the invention. Examples of such sub-classes ofpreferred compounds according to the invention can be combined:

preferred features of A with preferred features of Z¹, Z², Z³, Z⁴, Z⁵,Z⁶, Z⁷, X, W, T, n and R;

preferred features of Z¹ with preferred features of A, Z², Z³, Z⁴, Z⁵,Z⁶, Z⁷, X, W, T, n and R;

preferred features of Z² with preferred features of A, Z¹, Z³, Z⁴, Z⁵,Z⁶, Z⁷, X, W, T, n and R;

preferred features of Z³ with preferred features of A, Z¹, Z², Z⁴, Z⁵,Z⁶, Z⁷, X, W, T, n and R;

preferred features of Z⁴ with preferred features of A, Z¹, Z², Z³, Z⁵,Z⁶, Z⁷, X, W, T, n and R;

preferred features of Z⁵ with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁶, Z⁷, X, W, T, n and R;

preferred features of Z⁶ with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁵, Z⁷, X, W, T, n and R;

preferred features of Z⁷ with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁵, Z⁶, X, W, T, n and R;

preferred features of X with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁵, Z⁶, Z⁷, W, T, n and R;

preferred features of W with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁵, Z⁶, Z⁷, X, T, n and R;

preferred features of T with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁵, Z⁶, Z⁷, X, W, n and R;

preferred features of n with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁵, Z⁶, Z⁷, X, W, T and R;

preferred features of R with preferred features of A, Z¹, Z², Z³, Z⁴,Z⁵, Z⁶, Z⁷, X, W, T and n;

In these combinations of preferred features of the substituents of thecompounds according to the invention, the said preferred features canalso be selected among the more preferred features of each of A, Z¹, Z²,Z³, Z⁴, Z⁵, Z⁶, Z⁷, X, W, T, n and R, so as to form most preferredsubclasses of compounds according to the invention.

The present invention also relates to a process for the preparation ofthe compound of formula (I).

Thus, according to a further aspect of the present invention there isprovided a process P1 for the preparation of a compound of formula (I)as herein-defined and wherein T represents O and that comprises reactinga 3-(2-pyridyl)-1aminopropane derivative of formula (II) or its oxa,this or aza analogue or one of its salt:

wherein X, n, W, Z³, Z⁴, Z⁵, Z⁶ and Z⁷ are as herein-defined; with acarboxylic acid derivative of the formula (III)

wherein A is as herein-defined and L¹ represents a leaving groupselected in the list consisting of a halogen atom, a hydroxyl group,—OR^(b), —OC(═O)R^(b), R^(b) being a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, abenzyl, 4-methoxybenzyl or pentafluorophenyl group, or a group offormula O—C(═O)A; in the presence of a catalyst and in the presence of acondensing agent in case L¹ represents a hydroxyl group.

The process according to the present invention is conducted in thepresence of a catalyst. Suitable catalyst may be selected in the listconsisting of 4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole ordimethylformamide.

In case L¹ represents a hydroxy group, the process according to thepresent invention is conducted in the presence of condensing agent.Suitable condensing agent may be selected in the list consisting of acidhalide former, such as phosgene, phosphorous tribromide, phosphoroustrichloride, phosphorous-pentachloride, phosphorous trichloride oxide orthionyl chloride; anhydride former, such as ethyl chloroformate, methylchloroformate, isopropyl chloroformate, isobutyl chloroformate ormethanesulfonyl-chloride; carbodiimides, such asN,N′-dicyclohexylcarbodiimide (DCC) or other customary condensingagents, such as phosphorous pentoxide, polyphosphoric acid,N,N′-carbonyl-diimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloromethane,4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate or bromo-tripyrrolidino-phosphonium-hexafluorophosphate.

According to a further aspect according to the invention, there isprovided a process P2 for the preparation of a compound of formula (I)wherein T represents S, starting from a compound of formula (I) whereinT represents O and illustrated according to the following reactionscheme:

wherein X, n, W, Z³, Z⁴, Z⁵, Z⁶, Z⁷ and A are as herein-defined, in theoptional presence of a catalytic or stoechiometric or more, quantity ofa base such as an inorganic and organic base. Preference is given tousing alkali metal carbonates, such as sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate; heterocyclicaromatic bases, such as pyridine, picoline, lutidine, collidine; andalso tertiary amines, such as trimethylamine, triethylamine,tributylamine, N,N-dimethylaniline, N,N-dimethylaminopyridine orN-methylpiperidine.

Process P2 according to the invention can be performed in the presenceof a thionating agent.

Starting amide derivatives of formula (I) can be prepared according toprocesses P1.

Suitable thionating agents for carrying out process P2 according to theinvention can be sulphur (S), sulfhydric acid (H₂S), sodium sulfide(Na₂S), sodium hydrosulfide (NaHS), boron trisulfide (B₂S₃),bis(diethylaluminium) sulfide ((AlEt₂)₂S), ammonium sulfide ((NH₄)₂S),phosphorous pentasulfide (P₂S₅), Lawesson's reagent(2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) ora polymer-supported thionating reagent such as described in J. Chem.Soc. Perkin 1, (2001), 358.

The compound according to the present invention can be preparedaccording to the general processes of preparation described above. Itwill nevertheless be understood that, on the basis of his generalknowledge and of available publications, the skilled worker will be ableto adapt this method according to the specifics of each of thecompounds, which it is desired to synthesise.

Still in a further aspect, the present invention relates to compounds offormula (II) useful as intermediate compounds or materials for theprocess of preparation according to the invention.

The present invention thus provides compounds of formula (II):

wherein X, n, W and Z³, Z⁴, Z⁵, Z⁶, Z⁷ are as herein-defined,

On the basis of the present description and his general knowledge and ofavailable publications, the skilled person can prepare intermediatecompound of formula (II) according to the present invention.

In a further aspect, the present invention also relates to a fungicidecomposition comprising an effective and non-phytotoxic amount of anactive compound of formula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention that is sufficient to control ordestroy the fungi present or liable to appear on the cropsand that doesnot entail any appreciable symptom of phytotoxicity for the said crops.Such an amount can vary within a wide range depending on the fungus tobe controlled, the type of crop, the climatic conditions and thecompounds included in the fungicide composition according to theinvention. This amount can be determined by systematic field trials thatare within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) as herein defined and an agriculturallyacceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural orsynthetic, organic or inorganic compound with that the active compoundof formula (I) is combined or associated to make it easier to apply,notably to the parts of the plant. This support is thus generally inertand should be agriculturally acceptable. The support can be a solid or aliquid. Examples of suitable supports include clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilisers, water,alcohols, in particular butanol, organic solvents, mineral and plantoils and derivatives thereof. Mixtures of such supports can also beused.

The composition according to the invention can also comprise additionalcomponents. In particular, the composition can further comprise asurfactant. The surfactant can be an emulsifier, a dispersing agent or awetting agent of ionic or non-ionic type or a mixture of suchsurfactants. Mention can be made, for example, of polyacrylic acidsalts, lignosulphonic acid salts, phenolsulphonic ornaphthalenesulphonic acid salts, polycondensates of ethylene oxide withfatty alcohols or with fatty acids or with fatty amines, substitutedphenols (in particular alkylphenols or arylphenols), salts ofsulphosuccinic acid esters, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols,fatty acid esters of polyolsand derivatives of the above compoundscontaining sulphate, sulphonate and phosphate functions. The presence ofat least one surfactant is generally essential when the active compoundand/or the inert support are water-insoluble and when the vector agentfor the application is water. Preferably, surfactant content can becomprised from 5% to 40% by weight of the composition.

Optionally, additional components can also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active compoundscan be combined with any solid or liquid additive, that complies withthe usual formulation techniques.

In general, the composition according to the invention can contain from0.05 to 99% by weight of active compound, preferably 10 to 70% byweight.

Compositions according to the invention can be used in various formssuch as aerosol dispenser, capsule suspension, cold fogging concentrate,dustable powder, emulsifiable concentrate, emulsion oil in water,emulsion water in oil, encapsulated granule, fine granule, flowableconcentrate for seed treatment, gas (under pressure),gas generatingproduct, granule, hot fogging concentrate, macrogranule, microgranule,oil dispersible powder, oil miscible flowable concentrate, oil miscibleliquid, paste, plant rodlet, powder for dry seed treatment, seed coatedwith a pesticide, soluble concentrate, soluble powder, solution for seedtreatment, suspension concentrate (flowable concentrate), ultra lowvolume (ULV) liquid, ultra low volume (ULV) suspension, waterdispersible granules or tablets, water dispersible powder for slurrytreatment, water soluble granules or tablets, water soluble powder forseed treatment and wettable powder. These compositions include not onlycompositions that are ready to be applied to the plant or seed to betreated by means of a suitable device, such as a spraying or dustingdevice, but also concentrated commercial compositions that must bediluted before application to the crop.

The compounds according to the invention can also be mixed with one ormore insecticide, fungicide, bactericide, attractant, acaricide orpheromone active substance or other compounds with biological activity.The mixtures thus obtained have normally a broadened spectrum ofactivity. The mixtures with other fungicide compounds are particularlyadvantageous.

Examples of suitable fungicide mixing partners can be selected in thefollowing lists:

(1) Inhibitors of the nucleic acid synthesis, for example benalaxyl,benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl,hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl and oxolinic acid.

(2) Inhibitors of the mitosis and cell division, for example benomyl,carbendazim, chlorfenazole, diethofencarb, ethaboxam, fuberidazole,pencycuron, thiabendazole, thiophanate, thiophanate-methyl and zoxamide.

(3) Inhibitors of the respiration, for example diflumetorim asCI-respiration inhibitor; bixafen, boscalid, carboxin, fenfuram,flutolanil, fluopyram, furametpyr, furmecyclox, isopyrazam (mixture ofsyn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate1RS,4SR,9SR), isopyrazam (syn epimeric racemate 1RS,4SR,9RS), isopyrazam(syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimeric enantiomer1S,4R,9S), isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), isopyrazam(anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimericenantiomer 1S,4R,9R), mepronil, oxycarboxin, penflufen, penthiopyrad,sedaxane, thifluzamide as CII-respiration inhibitor; amisulbrom,azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadone,fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin,orysastrobin, picoxystrobin, pyraclostrobin, pyraoxystrobin,pyrametostrobin, pyribencarb, trifloxystrobin as CIII-respirationinhibitor.

(4) Compounds capable to act as an uncoupler, like for examplebinapacryl, dinocap, fluazinam and meptyldinocap.

(5) Inhibitors of the ATP production, for example fentin acetate, fentinchloride, fentin hydroxide, and silthiofam.

(6) Inhibitors of the amino acid and/or protein biosynthesis, forexample andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim and pyrimethanil.

(7) Inhibitors of the signal transduction, for example fenpiclonil,fludioxonil and quinoxyfen.

(8) Inhibitors of the lipid and membrane synthesis, for examplebiphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, iprobenfos,iprodione, isoprothiolane, procymidone, propamocarb, propamocarbhydrochloride, pyrazophos, tolclofos-methyl and vinclozolin.

(9) Inhibitors of the ergosterol biosynthesis, for example aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol,pefurazoate, penconazole, piperalin, prochloraz, propiconazole,prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole,spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon,triadimenol, tridemorph, triflumizole, triforine, triticonazole,uniconazole, viniconazole and voriconazole.

(10) Inhibitors of the cell wall synthesis, for example benthiavalicarb,dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins,polyoxorim, prothiocarb, validamycin A, and valifenalate.

(11) Inhibitors of the melanine biosynthesis, for example carpropamid,diclocymet, fenoxanil, phthalide, pyroquilon and tricyclazole.

(12) Compounds capable to induce a host defence, like for exampleacibenzolar-S-methyl, probenazole, and tiadinil.

(13) Compounds capable to have a multisite action, like for examplebordeaux mixture, captafol, captan, chlorothalonil, copper naphthenate,copper oxide, copper oxychloride, copper preparations such as copperhydroxide, copper sulphate, dichlofluanid, dithianon, dodine, dodinefree base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate,iminoctadine, iminoctadine albesilate, iminoctadine triacetate,mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper,propamidine, propineb, sulphur and sulphur preparations includingcalcium polysulphide, thiram, tolylfluanid, zineb and ziram.

(14) Further compounds like for example2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one,ethyl(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate,N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl}1H-imidazole-1-carbothioate,N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N²-(methylsulfonyl)valinamide,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,5-amino-1,3,4-thiadiazole-2-thiol, propamocarb-fosetyl,1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl1H-imidazole-1-carboxylate,1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2-phenylphenol and salts,3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,3,4,5-trichloropyridine-2,6-dicarbonitrile,3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,quinolin-8-ol, quinolin-8-ol sulfate (2:1) (salt), tebufloquin,5-methyl-6-octyl-3,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,5-ethyl-6-octyl-3,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,ametoctradin, benthiazole, bethoxazin, capsimycin, carvone,chinomethionat, chloroneb, cufraneb, cyflufenamid, cymoxanil,cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, dicloran,difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomate,ferimzone, flumetover, fluopicolide, fluoroimide, flusulfamide,flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium,hexachlorobenzene, irumamycin, isotianil, methasulfocarb, methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylate,methyl isothiocyanate, metrafenone,(5-chloro-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,mildiomycin, tolnifanide,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl,octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts,phenazine-1-carboxylic acid, phenothrin, phosphorous acid and its salts,propamocarb fosetylate, propanosine-sodium, proquinazid, pyrrolnitrine,quintozene, S-prop-2-en-1-yl5-amino-2-(1-methylethyl)-4-(2-methylphenyl)-3-oxo-2,3-dihydro-1H-pyrazole-1-carbothioate,tecloftalam, tecnazene, triazoxide, trichlamide,5-chloro-N′-phenyl-N′-prop-2-yn-1-ylthiophene-2-sulfonohydrazide,zarilamid,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamideandpentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound can also beparticularly advantageous. Examples of suitable bactericide mixingpartners can be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulphate and other copper preparations.

The compounds of formula (I) and the fungicide composition according tothe invention can be used to curatively or preventively control thephytopathogenic fungi of plants or crops. Thus, according to a furtheraspect of the invention, there is provided a method for curatively orpreventively controlling the phytopathogenic fungi of plants or cropscharacterised in that a compound of formula (I) or a fungicidecomposition according to the invention is applied to the seed, the plantor to the fruit of the plant or to the soil wherein the plant is growingor wherein it is desired to grow.

The method of treatment according to the invention can also be useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the invention can also be useful to treat theoverground parts of the plant such as trunks, stems or stalks, leaves,flowers and fruit of the concerned plant.

Among the plants that can be protected by the method according to theinvention, mention can be made of cotton; flax; vine; fruit or vegetablecrops such as Rosaceae sp. (for instance pip fruit such as apples andpears, but also stone fruit such as apricots, almonds and peaches),Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp.,Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceaesp., Musaceae sp. (for instance banana trees and plantins), Rubiaceaesp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemonsoranges and grapefruit); Solanaceae sp. (for instance tomatoes),Liliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp.,Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp.(for instance peas), Rosaceae sp. (for instance strawberries); majorcrops such as Graminae sp. (for instance maize, lawn or cereals such aswheat, rye, rice, barley and triticale), Asteraceae sp. (for instancesunflower), Cruciferae sp. (for instance colza), Fabacae sp. (forinstance peanuts), Papilionaceae sp. (for instance soybean), Solanaceaesp. (for instance potatoes), Chenopodiaceae sp. (for instancebeetroots), Elaeis sp. (for instance oil palm); horticultural and forestcrops; as well as genetically modified homologues of these crops.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants inwhich a heterologous gene has been stably integrated into the genome.The expression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, co suppression technology or RNAinterference—RNAi—technology). A heterologous gene that is located inthe genome is also called a transgene. A transgene that is defined byits particular location in the plant genome is called a transformationor transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the active compounds and compositions which can be usedaccording to the invention, better plant growth, increased tolerance tohigh or low temperatures, increased tolerance to drought or to water orsoil salt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, largerplant height, greener leaf color, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products are possible, which exceed theeffects which were actually to be expected.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect in plants.Accordingly, they are also suitable for mobilizing the defense system ofthe plant against attack by unwanted phytopathogenic fungi and/ormicroorganisms and/or viruses. This may, if appropriate, be one of thereasons of the enhanced activity of the combinations according to theinvention, for example against fungi. Plant-strengthening(resistance-inducing) substances are to be understood as meaning, in thepresent context, those substances or combinations of substances whichare capable of stimulating the defense system of plants in such a waythat, when subsequently inoculated with unwanted phytopathogenic fungiand/or microorganisms and/or viruses, the treated plants display asubstantial degree of resistance to these unwanted phytopathogenic fungiand/or microorganisms and/or viruses. In the present case, unwantedphytopathogenic fungi and/or microorganisms and/or viruses are to beunderstood as meaning phytopathogenic fungi, bacteria and viruses. Thus,the substances according to the invention can be employed for protectingplants against attack by the abovementioned pathogens within a certainperiod of time after the treatment. The period of time within whichprotection is effected generally extends from 1 to 10 days, preferably 1to 7 days, after the treatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozon exposure, highlight exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stress factors. Such plants are typicallymade by crossing an inbred male-sterile parent line (the female parent)with another inbred male-fertile parent line (the male parent). Hybridseed is typically harvested from the male sterile plants and sold togrowers. Male sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or males flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants is fully restored. This can be accomplished by ensuring that themale parents have appropriate fertility restorer genes which are capableof restoring the male fertility in hybrid plants that contain thegenetic determinants responsible for male-sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO2005/002324, WO 2006/021972 and U.S. Pat. No. 6,229,072). However,genetic determinants for male sterility can also be located in thenuclear genome. Male sterile plants can also be obtained by plantbiotechnology methods such as genetic engineering. A particularly usefulmeans of obtaining male-sterile plants is described in WO 1989/10396 inwhich, for example, a ribonuclease such as barnase is selectivelyexpressed in the tapetum cells in the stamens. Fertility can then berestored by expression in the tapetum cells of a ribonuclease inhibitorsuch as barstar (e.g. WO 1991/002069).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate through different means. Forexample, glyphosate-tolerant plants can be obtained by transforming theplant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphatesynthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutantCT7) of the bacterium Salmonella typhimurium (Comai et al., Science(1983), 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.(Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), thegenes encoding a Petunia EPSPS (Shah et al., Science (1986), 233,478-481), a Tomato EPSPS (Gasser et al., J. Biol. Chem. (1988),263,4280-4289), or an Eleusine EPSPS (WO 2001/66704). It can also be amutated EPSPS as described in for example EP-A 0837944, WO 2000/066746,WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also beobtained by expressing a gene that encodes a glyphosate oxido-reductaseenzyme as described in U.S. Pat. No. 5,776,760 and U.S. Pat. No.5,463,175. Glyphosate-tolerant plants can also be obtained by expressinga gene that encodes a glyphosate acetyl transferase enzyme as describedin for example WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO2007/024782. Glyphosate-tolerant plants can also be obtained byselecting plants containing naturally-occurring mutations of theabove-mentioned genes, as described in for example WO 2001/024615 or WO2003/013226.

Other herbicide resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedby expressing an enzyme detoxifying the herbicide or a mutant glutaminesynthase enzyme that is resistant to inhibition. One such efficientdetoxifying enzyme is an enzyme encoding a phosphinothricinacetyltransferase (such as the bar or pat protein from Streptomycesspecies). Plants expressing an exogenous phosphinothricinacetyltransferase are for example described in U.S. Pat. No. 5,561,236;U.S. Pat. No. 5,648,477; U.S. Pat. No. 5,646,024; U.S. Pat. No.5,273,894; U.S. Pat. No. 5,637,489; U.S. Pat. No. 5,276,268; U.S. Pat.No. 5,739,082; U.S. Pat. No. 5,908,810 and U.S. Pat. No. 7,112,665.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase(HPPD).

Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reactionin which para-hydroxyphenylpyruvate (HPP) is transformed intohomogentisate. Plants tolerant to HPPD-inhibitors can be transformedwith a gene encoding a naturally-occurring resistant HPPD enzyme, or agene encoding a mutated HPPD enzyme as described in WO 1996/038567, WO1999/024585 and WO 1999/024586. Tolerance to HPPD-inhibitors can also beobtained by transforming plants with genes encoding certain enzymesenabling the formation of homogentisate despite the inhibition of thenative HPPD enzyme by the HPPD-inhibitor. Such plants and genes aredescribed in WO 1999/034008 and WO 2002/36787. Tolerance of plants toHPPD inhibitors can also be improved by transforming plants with a geneencoding an enzyme prephenate dehydrogenase in addition to a geneencoding an HPPD-tolerant enzyme, as described in WO 2004/024928.

Still further herbicide resistant plants are plants that are madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides, as described for examplein Tranel and Wright, Weed Science (2002), 50, 700-712, but also, inU.S. Pat. No. 5,605,011, U.S. Pat. No. 5,378,824, U.S. Pat. No.5,141,870, and U.S. Pat. No. 5,013,659. The production ofsulfonylurea-tolerant plants and imidazolinone-tolerant plants isdescribed in U.S. Pat. No. 5,605,011; U.S. Pat. No. 5,013,659; U.S. Pat.No. 5,141,870; U.S. Pat. No. 5,767,361; U.S. Pat. No. 5,731,180; U.S.Pat. No. 5,304,732; U.S. Pat. No. 4,761,373; U.S. Pat. No. 5,331,107;U.S. Pat. No. 5,928,937; and U.S. Pat. No. 5,378,824; and internationalpublication WO 1996/033270. Other imidazolinone-tolerant plants are alsodescribed in for example WO 2004/040012, WO 2004/106529, WO 2005/020673,WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351, and WO2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants arealso described in for example WO 2007/024782.

Other plants tolerant to imidazolinone and/or sulfonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding as described for examplefor soybeans in U.S. Pat. No. 5,084,082, for rice in WO 1997/41218, forsugar beet in U.S. Pat. No. 5,773,702 and WO 1999/057965, for lettuce inU.S. Pat. No. 5,198,599, or for sunflower in WO 2001/065922.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, includes anyplant containing at least one transgene comprising a coding sequenceencoding:

-   -   1) an insecticidal crystal protein from Bacillus thuringiensis        or an insecticidal portion thereof, such as the insecticidal        crystal proteins listed by Crickmore et al., Microbiology and        Molecular Biology Reviews (1998), 62, 807-813, updated by        Crickmore et al. (2005) at the Bacillus thuringiensis toxin        nomenclature, online at:        http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or        insecticidal portions thereof, e.g., proteins of the Cry protein        classes Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or        insecticidal portions thereof; or    -   2) a crystal protein from Bacillus thuringiensis or a portion        thereof which is insecticidal in the presence of a second other        crystal protein from Bacillus thuringiensis or a portion        thereof, such as the binary toxin made up of the Cry34 and Cry35        crystal proteins (Moellenbeck et al., Nat. Biotechnol. (2001),        19, 668-72; Schnepf et al., Applied Environm. Microbiol. (2006),        71, 1765-1774); or    -   3) a hybrid insecticidal protein comprising parts of different        insecticidal crystal proteins from Bacillus thuringiensis, such        as a hybrid of the proteins of 1) above or a hybrid of the        proteins of 2) above, e.g., the Cry1A.105 protein produced by        corn event MON98034 (WO 2007/027777); or    -   4) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation, such as the        Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A        protein in corn event MIR604;    -   5) an insecticidal secreted protein from Bacillus thuringiensis        or Bacillus cereus, or an insecticidal portion thereof, such as        the vegetative insecticidal (VIP) proteins listed at:        http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html,        e.g., proteins from the VIP3Aa protein class; or    -   6) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a second        secreted protein from Bacillus thuringiensis or B. cereus, such        as the binary toxin made up of the VIP1A and VIP2A proteins (WO        1994/21795); or    -   7) a hybrid insecticidal protein comprising parts from different        secreted proteins from Bacillus thuringiensis or Bacillus        cereus, such as a hybrid of the proteins in 1) above or a hybrid        of the proteins in 2) above; or    -   8) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation (while still        encoding an insecticidal protein), such as the VIP3Aa protein in        cotton event COT102.

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 8. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 8, to expand the range oftarget insect species affected when using different proteins directed atdifferent target insect species, or to delay insect resistancedevelopment to the plants by using different proteins insecticidal tothe same target insect species but having a different mode of action,such as binding to different receptor binding sites in the insect.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants include:

-   -   a. plants which contain a transgene capable of reducing the        expression and/or the activity of poly(ADP-ribose)polymerase        (PARP) gene in the plant cells or plants as described in WO        2000/004173 or WO2006/045633 or PCT/EP07/004142.    -   b. plants which contain a stress tolerance enhancing transgene        capable of reducing the expression and/or the activity of the        PARG encoding genes of the plants or plants cells, as described        e.g. in WO 2004/090140.    -   c. plants which contain a stress tolerance enhancing transgene        coding for a plant-functional enzyme of the nicotinamide adenine        dinucleotide salvage synthesis pathway including nicotinamidase,        nicotinate phosphoribosyltransferase, nicotinic acid        mononucleotide adenyl transferase, nicotinamide adenine        dinucleotide synthetase or nicotine amide        phosphoribosyltransferase as described e.g. in WO2006/032469 or        WO 2006/133827 or PCT/EP07/002433.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   -   1) transgenic plants which synthesize a modified starch, which        in its physical-chemical characteristics, in particular the        amylose content or the amylose/amylopectin ratio, the degree of        branching, the average chain length, the side chain        distribution, the viscosity behaviour, the gelling strength, the        starch grain size and/or the starch grain morphology, is changed        in comparison with the synthesised starch in wild type plant        cells or plants, so that this is better suited for special        applications. Said transgenic plants synthesizing a modified        starch are disclosed, for example, in EP 0571427, WO        1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO        1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO        1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO        1998/40503, WO99/58688, WO 1999/58690, WO 1999/58654, WO        2000/008184, WO 2000/008185, WO 2000/008175, WO 2000/28052, WO        2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO        2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO        2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO        2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO        2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO        2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP        07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO        2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO        1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO        1999/53072, U.S. Pat. No. 6,734,341, WO 2000/11192, WO        1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO        2005/002359, U.S. Pat. No. 5,824,790, U.S. Pat. No. 6,013,861,        WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026, WO        1997/20936.    -   2) transgenic plants which synthesize non starch carbohydrate        polymers or which synthesize non starch carbohydrate polymers        with altered properties in comparison to wild type plants        without genetic modification. Examples are plants producing        polyfructose, especially of the inulin and levan-type, as        disclosed in EP 0663956, WO 1996/001904, WO 1996/021023, WO        1998/039460, and WO 1999/024593, plants producing alpha 1,4        glucans as disclosed in WO 1995/031553, US 2002/031826, U.S.        Pat. No. 6,284,479, U.S. Pat. No. 5,712,107, WO 1997/047806, WO        1997/047807, WO 1997/047808 and WO 2000/014249, plants producing        alpha-1,6 branched alpha-1,4-glucans, as disclosed in WO        2000/73422, plants producing alternan, as disclosed in WO        2000/047727, EP 06077301.7, U.S. Pat. No. 5,908,975 and EP        0728213,    -   3) transgenic plants which produce hyaluronan, as for example        disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO        2007/039316, JP 2006/304779, and WO 2005/012529.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as cotton plants, with altered fibercharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants contain a mutation imparting such alteredfiber characteristics and include:

-   -   a) Plants, such as cotton plants, containing an altered form of        cellulose synthase genes as described in WO 1998/000549    -   b) Plants, such as cotton plants, containing an altered form of        rsw2 or rsw3 homologous nucleic acids as described in        WO2004/053219    -   c) Plants, such as cotton plants, with increased expression of        sucrose phosphate synthase as described in WO 2001/017333    -   d) Plants, such as cotton plants, with increased expression of        sucrose synthase as described in WO02/45485    -   e) Plants, such as cotton plants, wherein the timing of the        plasmodesmatal gating at the basis of the fiber cell is altered,        e.g. through downregulation of fiberselective β 3 1,3-glucanase        as described in WO2005/017157    -   f) Plants, such as cotton plants, having fibers with altered        reactivity, e.g. through the expression of        N-acteylglucosaminetransferase gene including nodC and        chitinsynthase genes as described in WO2006/136351

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation or by selection of plants contain amutation imparting such altered oil characteristics and include:

-   -   a) Plants, such as oilseed rape plants, producing oil having a        high oleic acid content as described e.g. in U.S. Pat. No.        5,969,169, U.S. Pat. No. 5,840,946 or U.S. Pat. No. 6,323,392 or        U.S. Pat. No. 6,063,947    -   b) Plants such as oilseed rape plants, producing oil having a        low linolenic acid content as described in U.S. Pat. No.        6,270828, U.S. Pat. No. 6,169,190 or U.S. Pat. No. 5,965,755    -   c) Plant such as oilseed rape plants, producing oil having a low        level of saturated fatty acids as described e.g. in U.S. Pat.        No. 5,434,283

Particularly useful transgenic plants which may be treated according tothe invention are plants which comprise one or more genes which encodeone or more toxins, such as the following which are sold under the tradenames YIELD GARD® (for example maize, cotton, soya beans), KnockOut®(for example maize), BiteGard® (for example maize), Bt-Xtra® (forexample maize), StarLink® (for example maize), Bollgard® (cotton),Nucotn® (cotton), Nucotn 33B®(cotton), NatureGard® (for example maize),Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plantswhich may be mentioned are maize varieties, cotton varieties and soyabean varieties which are sold under the trade names Roundup Ready®(tolerance to glyphosate, for example maize, cotton, soya bean), LibertyLink® (tolerance to phosphinotricin, for example oilseed rape), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentionedinclude the varieties sold under the name Clearfield® (for examplemaize).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, orcombination of transformation events, that are listed for example in thedatabases from various national or regional regulatory agencies (see forexample http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

The composition according to the invention may also be used againstfungal diseases liable to grow on or inside timber. The term “timber”means all types of species of wood, and all types of working of thiswood intended for construction, for example solid wood, high-densitywood, laminated wood, and plywood. The method for treating timberaccording to the invention mainly consists in contacting one or morecompounds according to the invention or a composition according to theinvention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

Among the diseases of plants or crops that can be controlled by themethod according to the invention, mention can be made of:

-   -   Powdery mildew diseases such as:    -   Blumeria diseases, caused for example by Blumeria graminis;    -   Podosphaera diseases, caused for example by Podosphaera        leucotricha;    -   Sphaerotheca diseases, caused for example by Sphaerotheca        fuliginea;    -   Uncinula diseases, caused for example by Uncinula necator;    -   Rust diseases such as:    -   Gymnosporangium diseases, caused for example by Gymnosporangium        sabinae;    -   Hemileia diseases, caused for example by Hemileia vastatrix;    -   Phakopsora diseases, caused for example by Phakopsora pachyrhizi        or Phakopsora meibomiae;    -   Puccinia diseases, caused for example by Puccinia recondita;    -   Uromyces diseases, caused for example by Uromyces        appendiculatus;    -   Oomycete diseases such as:    -   Albugo diseases caused for example by Albugo candida;    -   Bremia diseases, caused for example by Bremia lactucae;    -   Peronospora diseases, caused for example by Peronospora pisi        or P. brassicae;    -   Phytophthora diseases, caused for example by Phytophthora        infestans;    -   Plasmopara diseases, caused for example by Plasmopara viticola;    -   Pseudoperonospora diseases, caused for example by        Pseudoperonospora humuli or Pseudoperonospora cubensis;    -   Pythium diseases, caused for example by Pythium ultimum;    -   Leafspot, leaf blotch and leaf blight diseases such as:    -   Alternaria diseases, caused for example by Alternaria solani;    -   Cercospora diseases, caused for example by Cercospora beticola;    -   Cladiosporum diseases, caused for example by Cladiosporium        cucumerinum;    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus;    -   Colletotrichum diseases, caused for example by Colletotrichum        lindemuthanium;    -   Cycloconium diseases, caused for example by Cycloconium        oleaginum;    -   Diaporthe diseases, caused for example by Diaporthe citri;    -   Drechslera, Syn: Helminthosporium) or Cochliobolus miyabeanus;    -   Elsinoe diseases, caused for example by Elsinoe fawcettii;    -   Gloeosporium diseases, caused for example by Gloeosporium        laeticolor;    -   Glomerella diseases, caused for example by Glomerella cingulata;    -   Guignardia diseases, caused for example by Guignardia bidwelli;    -   Leptosphaeria diseases, caused for example by Leptosphaeria        maculans; Leptosphaeria nodorum;    -   Magnaporthe diseases, caused for example by Magnaporthe grisea;    -   Mycosphaerella diseases, caused for example by Mycosphaerella        graminicola;    -   Mycosphaerella arachidicola; Mycosphaerella fijiensis;    -   Phaeosphaeria diseases, caused for example by Phaeosphaeria        nodorum;    -   Pyrenophora diseases, caused for example by Pyrenophora teres;    -   Ramularia diseases, caused for example by Ramularia collo-cygni;    -   Rhynchosporium diseases, caused for example by Rhynchosporium        secalis;    -   Septoria diseases, caused for example by Septoria apii or        Septoria lycopercisi;    -   Typhula diseases, caused for example by Typhula incamata;    -   Venturia diseases, caused for example by Venturia inaequalis;    -   Root and stem diseases such as:    -   Corticium diseases, caused for example by Corticium graminearum;    -   Fusarium diseases, caused for example by Fusarium oxysporum;    -   Gaeumannomyces diseases, caused for example by Gaeumannomyces        graminis;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Sarocladium diseases caused for example by Sarocladium oryzae;    -   Sclerotium diseases caused for example by Sclerotium oryzae;    -   Tapesia diseases, caused for example by Tapesia acuformis;    -   Thielaviopsis diseases, caused for example by Thielaviopsis        basicola;    -   Ear and panicle diseases including maize cob, such as:    -   Alternaria diseases, caused for example by Alternaria spp.;    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Cladosporium diseases, caused for example by Cladosporium spp.;    -   Claviceps diseases, caused for example by Claviceps purpurea;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Monographella diseases, caused for example by Monographella        nivalis;    -   Smut and bunt diseases such as:    -   Sphacelotheca diseases, caused for example by Sphacelotheca        reiliana;    -   Tilletia diseases, caused for example by Tilletia caries;    -   Urocystis diseases, caused for example by Urocystis occulta;    -   Ustilago diseases, caused for example by Ustilago nuda;    -   Fruit rot and mould diseases such as:    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Botrytis diseases, caused for example by Botrytis cinerea;    -   Penicillium diseases, caused for example by Penicillium        expansum;    -   Rhizopus diseases caused by example by Rhizopus stolonifer    -   Sclerotinia diseases, caused for example by Sclerotinia        sclerotiorum;    -   Verticilium diseases, caused for example by Verticilium        alboatrum;    -   Seed and soil borne decay, mould, wilt, rot and damping-off        diseases such as:    -   Alternaria diseases, caused for example by Alternaria        brassicicola    -   Aphanomyces diseases, caused for example by Aphanomyces        euteiches    -   Ascochyta diseases, caused for example by Ascochyta lentis    -   Aspergillus diseases, caused for example by Aspergillus flavus    -   Cladosporium diseases, caused for example by Cladosporium        herbarum    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus    -   (Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium);    -   Colletotrichum diseases, caused for example by Colletotrichum        coccodes;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Macrophomina diseases, caused for example by Macrophomina        phaseolina    -   Monographella diseases, caused for example by Monographella        nivalis;    -   Penicillium diseases, caused for example by Penicillium expansum    -   Phoma diseases, caused for example by Phoma lingam    -   Phomopsis diseases, caused for example by Phomopsis sojae;    -   Phytophthora diseases, caused for example by Phytophthora        cactorum;    -   Pyrenophora diseases, caused for example by Pyrenophora graminea    -   Pyricularia diseases, caused for example by Pyricularia oryzae;    -   Pythium diseases, caused for example by Pythium ultimum;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Rhizopus diseases, caused for example by Rhizopus oryzae    -   Sclerotium diseases, caused for example by Sclerotium rolfsii;    -   Septoria diseases, caused for example by Septoria nodorum;    -   Typhula diseases, caused for example by Typhula incarnata;    -   Verticillium diseases, caused for example by Verticillium        dahliae;    -   Canker, broom and dieback diseases such as:    -   Nectria diseases, caused for example by Nectria gaffigena;    -   Blight diseases such as:    -   Monilinia diseases, caused for example by Monilinia taxa;    -   Leaf blister or leaf curl diseases such as:    -   Exobasidium diseases caused for nexample by Exobasidium vexans;    -   Taphrina diseases, caused for example by Taphrina deformans;    -   Decline diseases of wooden plants such as:    -   Esca diseases, caused for example by Phaemoniella clamydospora,        Phaeomoniella clamydospora, Phaeoacremonium aleophilum and        Fomitiporia mediterranea;    -   Eutypa dyeback, caused for example by Eutypa lata;    -   Dutch elm disease, caused for example by Ceratocystsc ulmi;    -   Ganoderma diseases caused by example by Ganoderma boninense;    -   Diseases of flowers and Seeds such as:    -   Botrytis diseases, caused for example by Botrytis cinerea;    -   Diseases of tubers such as:    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Helminthosporium diseases, caused for example by        Helminthosporium solani.    -   Diseases of Tubers such as    -   Rhizoctonia diseases caused for example by Rhizoctonia solani;    -   Helminthosporium diseases caused for example by Helminthosporium        solani;    -   Club root diseases such as    -   Plasmodiophora diseases, caused for example by Plamodiophora        brassicae;    -   Diseases caused by Bacterial Organisms such as    -   Xanthomanas species for example Xanthomonas campestris pv.        oryzae;    -   Pseudomonas species for example Pseudomonas syringae pv.        lachrymans;    -   Erwinia species for example Erwinia amylovora.

The fungicide composition according to the invention can also be usedagainst fungal diseases liable to grow on or inside timber. The term“timber” means all types of species of woodand all types of working ofthis wood intended for construction, for example solid wood,high-density wood, laminated wood and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds according to the invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active compound usually applied in the method of treatmentaccording to the invention is generally and advantageously from 10 to800 g/ha, preferably from 50 to 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given asillustrative examples of the method according to the invention. A personskilled in the art will know how to adapt the application doses, notablyaccording to the nature of the plant or crop to be treated.

The fungicide composition according to the invention can also be used inthe treatment of genetically modified organisms with the compoundsaccording to the invention or the agrochemical compositions according tothe invention. Genetically modified plants are plants into genome ofthat a heterologous gene encoding a protein of interest has been stablyintegrated. The expression “heterologous gene encoding a protein ofinterest” essentially means genes that give the transformed plant newagronomic properties, or genes for improving the agronomic quality ofthe modified plant.

The compounds or mixtures according to the invention can also be usedfor the preparation of composition useful to curatively or preventivelytreat human or animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated withreference to the following table of compound examples and the followingpreparation or efficacy examples.

Table 1 illustrates in a non-limiting manner examples of compounds offormula (I) according to the invention.

In table 1, cPr means cyclopropyl.

In table 1, M+H (Apcl+) means the molecular ion peak plus 1 a.m.u.(atomic mass unit) as observed in mass spectroscopy via positiveatmospheric pressure chemical ionisation.

In the following table, the logP values were determined in accordancewith EEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18), using the methoddescribed below:

Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid andacetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (comprising 3to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

Lambda max values were determined in the maxima of the chromatographicsignals using the UV spectra from 190 nm to 400 nm.

TABLE 1

Example A T Z3 Z4 Z5 Z6 Z7 W

Mass (M + H) 1

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 469 2

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 486 3

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 415 4

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 468 5

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 468 6

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 433 7

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 487 8

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 451 9

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 527 10

O H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 431 11

S H H Me H cPr CH₂ 3-chloro-5- (trifluoromethyl) pyridin-2-yl 449

PREPARATION EXAMPLE 1 Preparation ofN-{4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-yl}-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide(compound 6) Step 1: Preparation ofN-{4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-yl}cyclo-propanamine

To a cooled solution of 5.54 ml (80 mmol) of cyclopropylamine and 2.86ml (50 mmol) of acetic acid, together with 5 g of 3 Å molecular sieves,in 100 ml of methanol, are added 5 g (20 mmol) of4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one. The reactionmixture is stirred for 3.5 hrs at reflux. The reaction mixture is thencooled to 0° C. and 1.88 g (30 mmol) of sodium cyanoborohydride areslowly added and the reaction mixture is further stirred for 2 hrs atreflux. The cooled reaction mixture is then filtered over a cake ofdiatomaceous earth. The cake is washed twice by 80 ml of methanol andthe combined methanolic extracts are concentrated under vacuum. 100 mlof water are then added to the residue and the pH is ajusted to 10 witha 1 N solution of sodium hydroxyde. The watery layer is extracted twicewith ethyl acetate (2×50 ml). The combined organic layers are washedtwice by brine and dried over magnesium sulfate to yield afterconcentration 5.02 g of a brown oil. Column chromatography (gradientheptane/ethyl acetate) yielded 3 g (51% yield) ofN-{4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-yl}cyclo-propanamineas a light-brown oil (M+H=293).

Step 2: Preparation ofN-{4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-yl}-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

At ambient temperature, a solution of 200 mg (1.12 mmol) of3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride in 1 ml oftetrahydrofurane is added dropwise to a solution of 300 mg (1.02 mmol)ofN-{4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-yl}cyclo-propanamineand 0.3 ml (2.15 mmol) of triethylamine in 5 ml of tetrahydrofurane. Thereaction mixture is stirred for 2 hrs at 80° C. The solvent is removedunder vacuum and 100 ml of water are then added to the residue. Thewatery layer is extracted twice with ethyl acetate (2×50 ml) and thecombined organic layers are successively washed by a 1 N solution ofHCl, a saturated solution of potassium carbonate and brine and driedover magnesium sulfate to yield after concentration 408 mg (92% yield)ofN-{4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-yl}-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideas a brown oil (M+H=433).

General Preparation: Thionation of an Aamide Derivative of Formula (I)on Chemspeed™ Apparatus

In a 13 ml Chemspeed™ vial is weighted 0.27 mmole of phosphorouspentasulfide (P₂S₅). 3 ml of a 0.18 molar solution of the amide (I)(0.54 mmole) in dioxane is added and the mixture is heated at reflux fortwo hours. The temperature is then cooled to 80° C. and 2.5 ml of waterare added. The mixture is heated at 80° C. for one more hour. 2 ml ofwater are then added and the reaction mixture is extracted twice by 4 mlof dichloromethane. The organic phase is deposited on a basic aluminacardridge (2 g) and eluted twice by 8 ml of dichloromethane. Thesolvents are removed and the crude thioamide is analyzed by LCMS andNMR. Insufficiently pure compounds are further purified by preparativeLCMS.

EXAMPLE A In Vivo Test on Pyrenophora (Barley)/Preventive

-   -   Solvent: 49 parts by weight of N,N-Dimethylformamide    -   Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Pyrenophora teres. The plants remain for 48 hours inan incubation cabinet at 22° C. and a relative atmospheric humidity of100%. Then the plants are placed in a greenhouse at a temperature ofapproximately 20° C. and a relative atmospheric humidity ofapproximately 80%.

The test is evaluated 7-9 days after the inoculation. 0% means anefficacy which corresponds to that of the control while an efficacy of100% means that no disease is observed.

In this test the following compounds according to the invention showedefficacy of 70% or even higher at a concentration of 500 ppm of activeingredient: 1, 2, 4, 5, 7, 8, 9 and 10.

EXAMPLE B In Vivo Test on Septoria (Wheat)/Protective

Solvent: 50 parts by weight of N,N-Dimethylacetamid

Emulsifier: 1 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with a stated amount of solvent, and theconcentrate is diluted with water and the stated amount of emulsifier tothe desired concentration.

To test for protective activity, young wheat plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Septoria tritici. The plants aresubsequently placed for 2 days in an incubation chamber at 100% relativeatmospheric humidity and 20° C. After that, the plants are than placedunder an incubation cabin at 100% relative atmospheric humidity and 15°C. for 2,5 days.

After incubation the plants are than placed in a greenhouse chamber at80% relative atmospheric humidity and 15° C.

The test is evaluated 21 days after inoculation. 0% means an efficacywith corresponds to that of the control while an efficacy of 100% meansthat no disease is observed.

In this test the following compounds according to the invention showedefficacy of 70% or even higher at a concentration of 1000 ppm of activeingredient: 1 and 4.

1. A compound of formula (I)

wherein A represents a carbo-linked, unsaturated or partially saturated,5-membered heterocyclyl group that can be substituted by up to fourgroups R; T represents O or S; W represents CZ¹Z², O, S, SO, SO₂ orN—R^(a); n represents 0, 1, 2, 3 or 4; X represents a halogen atom, anitro, a cyano, an isonitrile, a hydroxy, an amino, a sulfanyl, apentafluoro-λ⁶-sulfanyl, a formyl, a formyloxy, a formylamino, acarboxy, a carbamoyl, a N-hydroxycarbamoyl, a carbamate, a(hydroxyimino)-C₁-C₆-alkyl, a C₁-C₈-halogenoalkyl having 1 to 9 halogenatoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-halogenoalkenylcomprising up to 9 halogen atoms that can be the same or different, aC₂-C₈-alkynyl, a C₂-C₈-halogenoalkynyl comprising up to 9 halogen atomsthat can be the same or different, a C₁-C₈-alkylamino, adi-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy having 1 to9 halogen atoms, a C₁-C₈-alkoxy-C₁-C₈-alkyl, aC₁-C₈-alkoxy-C₁-C₈-alkoxy, a C₁-C₈-alkylsulfanyl, aC₁-C₈-halogenoalkylsulfanyl having 1 to 9 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 9 halogenatoms, a C₂-C₈alkynyloxy, a C₂-C₈-halogenoalkynyloxy having 1 to 9halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₇-cycloalkyl-C₂-C₈alkenyl, aC₃-C₇-cycloalkyl-C₂-C₈-alkynyl, a C₃-C₈-halogenocycloalkyl having 1 to 9halogen atoms, a C₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl, aC₁-C₈-alkyl-C₃-C₇-cycloalkyl, a C₆-C₁₄-bicycloalkyl, aC₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to 9 halogenatoms, a C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aN—C₁-C₈-alkyloxycarbamoyl, a C₁-C₈-alkoxycarbamoyl, aN—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, aC₁-C₈-halogenoalkoxy carbonyl having 1 to 9 halogen atoms, aC₁-C₈-alkylcarbonyloxy, a C₁-C₈-halogenoalkylcarbonyloxy having 1 to 9halogen atoms, a C₁-C₈-alkylcarbonylamino, aC₁-C₈-halogenoalkylcarbonylamino having 1 to 9 halogen atoms, aC₁-C₈-alkylaminocarbonyloxy, a di-C₁-C₈-alkylaminocarbonyloxy, aC₁-C₈-alkyloxycarbonyloxy, a C₁-C₈-alkylsulphenyl, aC₁-C₈-halogenoalkylsulphenyl having 1 to 9 halogen atoms, aC₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinyl having 1 to 9halogen atoms, a C₁-C₈-alkylsulphonyl, a C₁-C₈-halogenoalkylsulphonylhaving 1 to 9 halogen atoms, a C₁-C₈-alkoxyimino, a(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, a(C₂-C₈-alkenyloxyimino)-C_(l)-C₈-alkyl, a(C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a (benzyloxyimino)-C₁ -C₈-alkyl, atri(C₁-C₈-alkyl)silyl, a tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, a benzyloxythat can be substituted by up to 5 groups Q, a benzylsulfanyl that canbe substituted by up to 5 groups Q, a benzylamino that can besubstituted by up to 5 groups Q, an aryl that can be substituted by upto 5 groups Q, an aryloxy that can be substituted by up to 5 groups Q,an arylamino that can be substituted by up to 5 groups Q, anarylsulfanyl that can be substituted by up to 5 groups Q, anaryl-C₁-C₈-alkyl that can be substituted by up to 5 groups Q, anaryl-C₂-C₈-alkenyl that can be substituted by up to 5 groups Q, anaryl-C₂-C₈-alkynyl that can be substituted by up to 5 groups Q, anaryl-C₃-C₇-cycloalkyl that can be substituted by up to 5 groups Q, apyridinyl that can be substituted by up to 4 groups Q and a pyridinyloxythat can be substituted by up to 4 groups Q; Z¹ and Z² independentlyrepresent a hydrogen atom, a halogen atom, a C₁-C₈-halogenoalkyl having1 to 5 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; Z³ and Z⁴ are chosenindependently of each other as being a hydrogen atom, a halogen atom, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; Z⁵ and Z⁶independently represent a hydrogen atom, a C₁-C₈-halogenoalkyl having 1to 5 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; Z⁷ represents anon-substituted C₃-C₇-cycloalkyl or a C₃-C₇-cycloalkyl substituted by upto 10 atoms or groups that can be the same or different and that can beselected in the list consisting of halogen atoms; cyano; C₁-C₈-alkyl;C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; C₁-C₈-alkoxycarbonyl;C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that canbe the same or different; C₁-C₈-alkylaminocarbonyl;di-C₁-C₈-alkylaminocarbonyl; R^(a) represents a hydrogen atom;C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl;C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be thesame or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl;C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to9 halogen atoms that can be the same or different; formyl;C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9halogen atoms that can be the same or different; C₁-C₈-alkylsulphonyl;C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that canbe the same or different; aryl that can be substituted by up to 5 groupsQ; phenylmethylene that can be substituted by up to 7 groups Q;phenylsulphonyl that can be substituted by up to 5 groups Q; Qindependently represents a halogen atom; cyano; isonitrile; nitro;C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-alkynyl; C₁-C₈-alkoxy;C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkoxy-C₁-C₈-alkoxy;C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₂-C₈-halogenoalkenylcomprising up to 9 halogen atoms that can be the same or different;C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; C₁-C₈-halogenoalkylsulfanylcomprising up to 9 halogen atoms that can be the same or different;C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms thatcan be the same or different; tri(C₁-C₈)alkylsilyl andtri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; C₁-C₈-alkoxyimino;(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; R independently represents a hydrogenatom; halogen atom; cyano; isonitrile; nitro; amino; sulfanyl;pentafluoro-λ⁶-sulfanyl C₁-C₈-alkylamino; di-C₁-C₈-alkylamino;tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanylcomprising up to 9 halogen atoms that can be the same or different;C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenylcomprising up to 9 halogen atoms that can be the same or different;C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;C₂-C₈-alkenyloxy; C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl;C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₁-C₈-alkylsulphinyl;C₁-C₈-alkylsulphonyl; C₁-C₈alkoxyimino; (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;(benzyloxyimino)-C₁-C₈-alkyl; aryloxy; benzyloxy; benzylsulfanyl;benzylamino; aryl; halogenoaryloxy comprising up to 9 halogen atoms thatcan be the same or different; C₁-C₈-alkylcarbonyl;C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can bethe same or different; C₁-C₈-alkoxycarbonyl;C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that canbe the same or different; C₁-C₈-alkylaminocarbonyl;di-C₁-C₈-alkylaminocarbonyl; with the provisio that when W is oxygen andT is oxygen and n is greater or equal to 1 then X is not a halogen atom,a nitro, a cyano, an amino, a formyl, a (hydroxyimino)-C₁-C₆-alkyl, aC₁-C₆-alkyl, a C₁-C₆-halogenoalkyl, a C₂-C₆-alkenyl, aC₂-C₆-halogenoalkenyl, a C₂-C₆-alkynyl, a C₂-C₆-halogenoalkynyl, aC₁-C₆-alkylamino, a di-C₁-C₆-alkylamino, a C₁-C₆-alkoxy, aC₁-C₆-halogenoalkoxy, a C₁-C₆-alkoxy-C₁-C₆-alkyl, a C₁-C₆-alkylsulfanyl,a C₂-C₆-alkenyloxy, a C₂-C₆-halogenoalkenyloxy, a C₃-C₆-cycloalkyl, aC₃-C₆-cycloalkyl-C₂-C₆-alkenyl, a C₃-C₆-cycloalkyl-C₂-C₆-alkynyl, aC₃-C₆-halogenocycloalkyl, a C₃-C₆-cycloalkyl-C₃-C₆-cycloalkyl, aC₁-C₆-alkyl-C₃-C₆-cycloalkyl, a C₆-C₁₄-bicycloalkyl, aC₁-C₆-alkylcarbonyl, a C₁-C₆-alkylcarbonylamino, a(C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a tri(C₁-C₆-alkyl)silyl-C₁-C₆-alkyl, aphenyl that can be substituted by one or more groups G, a phenoxy thatcan be substituted by up one or more groups G, a phenyl-C₁-C₆-alkyl thatcan be substituted by one or more halogens, a phenyl-C₂-C₆-alkenyl thatcan be substituted by one or more halogens, a phenyl-C₂-C₆-alkynyl thatcan be substituted by one or more halogens, a phenyl-C₃-C₆-cycloalkylthat can be substituted by one or more halogens; each G independentlyrepresents a halogen, nitro, C₁-C₆-alkoxy, C₁-C₆-alkylsulfanyl,C₁-C₆-halogenoalkoxy, C₁-C₆-halogenoalkyl sulfanyl,tri(C₁-C₆-alkyl)silyl, (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl; as well as itssalts, N-oxydes, metallic complexes, metalloidic complexes and opticallyactive isomers.
 2. A compound according to claim 1 wherein A is selectedin the list consisting of: a heterocycle of formula (A¹)

wherein: R¹ to R³ that can be the same or different represent a hydrogenatom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A²)

wherein: R⁴ to R⁶ that can be the same or different represent a hydrogenatom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A³)

wherein: R⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to9 halogen atoms that can be the same or different; R⁸ represents ahydrogen atom or a C₁-C₅-alkyl; a heterocycle of formula (A⁴)

wherein: R⁹ to R¹¹ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl; amino; C₁-C₅-alkoxy;C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different or C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different; aheterocycle of formula (A⁵)

wherein: R¹² and R¹³ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogenatoms that can be the same or different; R¹⁴ represents a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A⁶)

wherein: R¹⁵ represents a hydrogen atom; a halogen atom; a cyano;C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; R¹⁶and R¹⁸ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C₅-alkoxycarbonyl; C₁-C₅-alkyl; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; R¹⁷ represent a hydrogen atom or C₁-C₅-alkyl; aheterocycle of formula (A⁷)

wherein: R¹⁹ represents a hydrogen atom or a C₁-C₅-alkyl R²⁰ to R²² thatcan be the same or different represent a hydrogen atom; a halogen atom;C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; a heterocycle of formula (A⁸)

wherein: R²³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; R²⁴ represents a hydrogen atom or C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A⁹)

wherein: R²⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; R²⁶ represents a hydrogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A¹⁰)

wherein: R²⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; R²⁸ represents a hydrogen atom; a halogen atom;C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; amino; C₁-C₅-alkylaminoor di(C₁-C₅-alkyl)amino; a heterocycle of formula (A¹¹)

wherein: R²⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; R³⁰ represents ahydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino; aheterocycle of formula (A¹²)

wherein: R³¹ represents a hydrogen atom or a C₁-C₅-alkyl R³² representsa hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; R³³represents a hydrogen atom; a halogen atom; a nitro; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; a heterocycle offormula (A¹³)

wherein: R³⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C3-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; R³⁵ represents a hydrogen atom; a halogen atom;C₁-C₅-alkyl; a cyano; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; C₁-C₅-alkylamino ordi(C₁-C₅-alkyl)amino; R³⁶ represents a hydrogen atom or C₁-C₅-alkyl; aheterocycle of formula (A¹⁴)

wherein: R³⁷ and R³⁸ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;C₁-C₅-alkoxy or a C₁-C₅-alkylsulphanyl; R³⁹ represents a hydrogen atomor C₁-C₅-alkyl; a heterocycle of formula (A¹⁵)

wherein: R⁴⁰ and R⁴¹ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; aheterocycle of formula (A¹⁶)

wherein: R⁴² and R⁴³ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different oramino; a heterocycle of formula (A¹⁷)

wherein: R⁴⁴ and R⁴⁵ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; aheterocycle of formula (A¹⁸)

wherein: R⁴⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; R⁴⁶ represents a hydrogen atom; a halogen atom;C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-alkylsulfanyl; a heterocycle offormula (A¹⁹)

wherein: R⁴⁹ and R⁴⁸ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; a heterocycle of formula (A²⁰)

wherein: R⁵⁰ and R⁵¹ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; a heterocycle of formula (A²¹)

wherein: R⁵² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different. a heterocycle of formula (A²²)

wherein: R⁵³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different. a heterocycle of formula (A²³)

wherein: R⁵⁴ and R⁵⁶ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; R⁵⁵represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula(A²⁴)

wherein: R⁵⁷ and R⁵⁹ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; R⁵⁸represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula(A²⁵)

wherein: R⁶⁰ and R⁶¹ that can be the same or different represent ahydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; R⁶²represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula(A²⁶)

wherein: R⁶⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; R⁶³ represents a hydrogen atom; a halogen atom;C₁-C₅-alkyl; a cyano; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; C₁-C₅-alkylamino ordi(C₁-C₅-alkyl)amino; R⁶⁴ represents a hydrogen atom or C₁-C₅-alkyl. 3.A compound according to claim 2 wherein A is selected in the listconsisting of A²; A⁶; A¹⁰ and A¹³.
 4. A compound according to claim 3wherein A represents A¹³ and wherein R³⁴ represents a C₁-C₅-alkyl,C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; R³⁵ represents a hydrogen atom or ahalogen atom and R³⁶ represents a C₁-C₅-alkyl.
 5. A compound accordingto claim 1 wherein W represents O or S.
 6. A compound according to claim1 wherein W represents CZ¹Z².
 7. A compound according to claim 1 whereinn represents 0, 1 or
 2. 8. A compound according to claim 1 wherein Xindependently represents a halogen atom; C₁-C₈-alkyl;C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkoxy orC₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different or wherein two consecutive substituents X togetherwith the phenyl ring form a substituted or non substituted1,3-benzodioxolyl; 1,2,3,4-tetrahydro-quinoxalinyl;3,4-dihydro-2H-1,4-benzoxazinyl; 1,4-benzodioxanyl; indanyl;2,3-dihydrobenzofuranyl; or indolinyl.
 9. A compound according to claim1 wherein Z¹ to Z⁶ independently represent a hydrogen atom or aC₁-C₈-alkyl.
 10. A compound according to claim 1 wherein Z⁷ represents aC₃-C₇ cycloalkyl substituted by up to 10 groups or atoms that can be thesame or different and that can be selected in the list consisting ofhalogen atoms; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₈-alkoxy orC₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different.
 11. A compound according to claim 10 wherein Z⁷represents a non-substituted C₃-C₇-cycloalkyl.
 12. A compound accordingto claim 11 wherein Z⁷ represents cyclopropyl.
 13. A compound accordingto claim 1 wherein R independently represents a hydrogen atom; halogenatom; cyano; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino;tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-alkylsulfanyl; amino, hydroxyl; nitro;C₁-C₈-alkoxycarbonyl; C₂-C₈-alkynyloxy.
 14. A compound of formula (II):

wherein W represents CZ¹Z², O, S, SO, SO₂ or N—R^(a); n represents 0, 1,2, 3 or 4; X represents a halogen atom, a nitro, a cyano, an isonitrile,a hydroxy, an amino, a sulfanyl, a pentafluoro-λ⁶-sulfanyl, a formyl, aformyloxy, a formylamino, a carboxy, a carbamoyl, a N-hydroxycarbamoyl,a carbamate, a (hydroxyimino)-C₁-C₆-alkyl, a C₁-C₈-halogenoalkyl having1 to 9 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be thesame or different, a C₂-C₈-alkynyl, a C₂-C₈-halogenoalkynyl comprisingup to 9 halogen atoms that can be the same or different, aC₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 9 halogen atoms, aC₁-C₈-alkoxy-C₁-C₈-alkyl, a C₁-C₈-alkoxy-C₁-C₈-alkoxy, aC₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanyl having 1 to 9 halogenatoms, a C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 9halogen atoms, a C₂-C₈-alkynyloxy, a C₂-C₈-halogenoalkynyloxy having 1to 9 halogen atoms, a C₃-C₈-cycloalkyl, aC₃-C₇-cycloalkyl-C₂-C₈-alkenyl, a C₃-C₇-cycloalkyl-C₂-C₈-alkynyl, aC₃-C₈-halogenocycloalkyl having 1 to 9 halogen atoms, aC₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl, a C₁-C₈-alkyl-C₃-C₇-cycloalkyl, aC₆-C₁₄-bicycloalkyl, a C₁-C₈-alkylcarbonyl, aC₁-C₈-halogenoalkylcarbonyl having 1 to 9 halogen atoms, aC₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aN—C₁-C₈-alkyloxycarbamoyl, a C₁-C₈-alkoxycarbamoyl, aN—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, aC₁-C₈-halogenoalkoxy carbonyl having 1 to 9 halogen atoms, aC₁-C₈-alkylcarbonyloxy, a C₁-C₈-halogenoalkylcarbonyloxy having 1 to 9halogen atoms, a C₁-C₈-alkylcarbonylamino, aC₁-C₈-halogenoalkylcarbonylamino having 1 to 9 halogen atoms, aC₁-C₈-alkylaminocarbonyloxy, a di-C₁-C₈-alkylaminocarbonyloxy, aC₁-C₈-alkyloxycarbonyloxy, a C₁-C₈-alkylsulphenyl, aC₁-C₈-halogenoalkylsulphenyl having 1 to 9 halogen atoms, aC₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinyl having 1 to 9halogen atoms, a C₁-C₈-alkylsulphonyl, a C₁-C₈-halogenoalkylsulphonylhaving 1 to 9 halogen atoms, a C₁-C₈-alkoxyimino, a(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, a (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl,a (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a (benzyloxyimino)-C₁-C₈-alkyl, atri(C₁-C₈-alkyl)silyl, a tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, a benzyloxythat can be substituted by up to 5 groups Q, a benzylsulfanyl that canbe substituted by up to 5 groups Q, a benzylamino that can besubstituted by up to 5 groups Q, an aryl that can be substituted by upto 5 groups Q, an aryloxy that can be substituted by up to 5 groups Q,an arylamino that can be substituted by up to 5 groups Q, anarylsulfanyl that can be substituted by up to 5 groups Q, anaryl-C₁-C₈-alkyl that can be substituted by up to 5 groups Q, anaryl-C₁-C₈-alkenyl that can be substituted by up to 5 groups Q, anaryl-C₂-C₈-alkynyl that can be substituted by up to 5 groups Q, anaryl-C₃-C₇-cycloalkyl that can be substituted by up to 5 groups Q, apyridinyl that can be substituted by up to 4 groups Q and a pyridinyloxythat can be substituted by up to 4 groups Q; Z¹ and Z² independentlyrepresent a hydrogen atom, a halogen atom, a C₁-C₈-halogenoalkyl having1 to 5 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; Z³ and Z⁴ are chosenindependently of each other as being a hydrogen atom, a halogen atom, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, aC₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; Z⁵ and Z⁶independently represent a hydrogen atom, a C₁-C₈-halogenoalkyl having 1to 5 halogen atoms, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-halogenoalkenyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkynyl having 1 to 5 halogen atoms; Z⁷ represents anon-substituted C₃-C₇-cycloalkyl or a C₃-C₇-cycloalkyl substituted by upto 10 atoms or groups that can be the same or different and that can beselected in the list consisting of halogen atoms; cyano; C₁-C₈-alkyl;halogenoalkyl comprising up to 9 halogen atoms that can be the same ordifferent; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogenatoms that can be the same or different; C₁-C₈-alkoxycarbonyl;C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that canbe the same or different; C₁-C₈-alkylaminocarbonyl;di-C₁-C₈-alkylaminocarbonyl; R^(a) represents a hydrogen atom;C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl;C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl;C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to9 halogen atoms that can be the same or different; formyl;C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9halogen atoms that can be the same or different; C₁-C₈-alkylsulphonyl;C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that canbe the same or different; aryl that can be substituted by up to 5 groupsQ; phenylmethylene that can be substituted by up to 7 groups Q;phenylsulphonyl that can be substituted by up to 5 groups Q; and Qindependently represents a halogen atom; cyano; isonitrile; nitro;C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-alkynyl; C₁-C₈-alkoxy;C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkoxy-C₁-C₈-alkoxy;C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₂-C₈-halogenoalkenylcomprising up to 9 halogen atoms that can be the same or different;C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; C₁-C₈-halogenoalkylsulfanylcomprising up to 9 halogen atoms that can be the same or different;C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms thatcan be the same or different; tri(C₁-C₈)alkylsilyl andtri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; C₁-C₈-alkoxyimino;(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl.
 15. A fungicide composition comprising,as an active ingredient, an effective amount of a compound of formula(I) according to claim 1 and an agriculturally acceptable support,carrier or filler.
 16. A method for controlling phytopathogenic fungi ofcrops, characterized in that an agronomically effective andsubstantially non-phytotoxic quantity of a compound according to claim 1is applied to the soil where plants grow or are capable of growing, tothe leaves or the fruit of plants or to the seeds of plants.
 17. Amethod for controlling phytopathogenic fungi of crops, characterized inthat an agronomically effective and substantially non-phytotoxicquantity of a composition according to claim 15 is applied to the soilwhere plants grow or are capable of growing, to the leaves or the fruitof plants or to the seeds of plants.